2989-99-3

Basic information

• Product Name: 1-(2-Chlorophenyl)-3-phenylurea
• Synonyms: 1-(2-Chlorophenyl)-3-phenylurea;1-Phenyl-3-(2-chlorophenyl)urea;N-(2-Chlorophenyl)-N'-phenylurea
• CAS NO: 2989-99-3
• Molecular Formula: C₁₃H₁₁ClN₂O
• Molecular Weight: 246.6922
• Mol File: 2989-99-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 287.1°Cat760mmHg
• Flash Point: 127.5°C
• Appearance: /
• Density: 1.356g/cm³
• Vapor Pressure: 0.00253mmHg at 25°C
• Refractive Index: 1.696
• CAS DataBase Reference: 1-(2-Chlorophenyl)-3-phenylurea(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-Chlorophenyl)-3-phenylurea(2989-99-3)
• EPA Substance Registry System: 1-(2-Chlorophenyl)-3-phenylurea(2989-99-3)

Safety Data

• Hazardous Substances Data: 2989-99-3(Hazardous Substances Data)

Usage

Description

1-(2-Chlorophenyl)-3-phenylurea, commonly known as diuron, is a widely used herbicide that functions by inhibiting photosynthesis in plants. It is characterized by its white crystalline solid appearance and is relatively insoluble in water with low volatility. Although it exhibits low toxicity to mammals, it can be harmful to aquatic organisms and poses a risk of water source contamination.

Uses

Used in Agricultural Industry:
1-(2-Chlorophenyl)-3-phenylurea is used as a herbicide for controlling weeds in various crops such as cotton, citrus fruits, and sugar cane. Its effectiveness in inhibiting photosynthesis makes it a valuable tool in enhancing crop yield and quality by reducing competition from unwanted plant growth.
However, due to its potential environmental impact on aquatic organisms and the risk of water source contamination, the use of diuron has been subject to regulatory restrictions in some countries. This highlights the need for responsible and sustainable use of the herbicide to minimize its negative effects on the environment.

InChI:InChI=1/C13H11ClN2O/c14-11-8-4-5-9-12(11)16-13(17)15-10-6-2-1-3-7-10/h1-9H,(H2,15,16,17)

Upstream product

• 103-71-9 phenyl isocyanate 
• 95-51-2 o-chloroaniline 
• 49747-51-5 o-chlorobenzoyl azide 
• 62-53-3 aniline 
• 1932-36-1 1-(2-chloro-phenyl)-3-phenyl-thiourea 
• 694-80-4 2-bromo-1-chlorobenzene 
• 64-10-8 phenyl carbamate 
• 103-72-0 phenyl isothiocyanate 
• 495-18-1 Benzohydroxamic acid 
• 3320-83-0 o-chlorophenyl isocyanate 
• 118-91-2 ortho-chlorobenzoic acid 
• 19226-36-9 3-phenyl-5H-1,4,2-dioxazol-5-one 
• 88-73-3 2-Chloronitrobenzene 

Downstream Products

• 862891-89-2 1-benzyl-1-(2-chlorophenyl)-3-phenylurea 

Relevant articles and documents

Nitroarenes as versatile building blocks for the synthesis of unsymmetrical urea derivatives and N-Arylmethyl-2-substituted benzimidazoles

In this contribution, a fast and simple method for the synthesis of unsymmetrical urea derivatives and N-arylmethyl-2-substituted benzimidazoles was developed starting from nitroarenes. The reaction of nitroarenes and phenyl isocyanate or phenyl isothiocyanate in tin (II) chloride dihydrate/choline chloride eutectic mixture afforded the expected urea and thiourea derivatives, while the reaction of different aldehydes with o-nitroaniline or 4-methoxy-2-nitroaniline shows a markedly high preference for the obtention of N-arylmethyl-2-substituted benzimidazoles over the 2-substituted analogues. This method offers a straightforward alternative to obtain the target compounds in good to excellent yields with short reaction times employing an operationally simple experimental set-up. Graphic abstract: [Figure not available: see fulltext.] A series of unsymmetrical urea and thiourea derivatives together with 1,2-disubstituted benzimidazoles are easily obtained in good yields starting from nitroarenes employing the eutectic mixture tin (II) chloride dihydrate/choline chloride as reductive reaction media.

Scalable, One-Pot, Microwave-Accelerated Tandem Synthesis of Unsymmetrical Urea Derivatives

We report a facile, microwave-accelerated, one-pot tandem synthesis of unsymmetrical ureas via a Curtius rearrangement. In this method, one-pot microwave irradiation of commercially available (hetero)aromatic acids and amines in the presence of diphenylphosphoryl azide enabled extremely rapid (1-5 min) construction of an array of unsymmetrical ureas in good to excellent yields. We demonstrate the utility of our method in the efficient, gram-scale synthesis of key biologically active compounds targeting the cannabinoid 1 and α7 nicotinic acetylcholine receptors.

Bromodimethylsulfonium bromide (BDMS)-mediated Lossen rearrangement: Synthesis of unsymmetrical ureas

Bromodimethylsulfonium bromide (BDMS) was found to be a very efficient reagent for Lossen rearrangement of hydroxamic acids to the corresponding isocyanates which were subsequently trapped in situ with various amines to afford unsymmetrical ureas in good to excellent yields (64-89%). The protocol is experimentally simple, mild, and represents valuable alternative to the existing methods for in situ activation of hydroxamic acids promoting Lossen rearrangement.